Treatment of fibrous materials



Patented May 26; 1942 TREATMENT OF FIBBOUS MATERIALS Paul C. Schroy, Darien, Coma, asslgnor to American Cyanamid Company, New York, N. Y., a

corporation of Maine Application January 17, 1939, Serial No. 251,337

No Drawing.

12 Claims.

This invention relates to softening fibrous materials which have been impregnated with thermosetting resins as in the crease proofing of rayon, cotton, wool, etc.

The use of various compounds, e. g., sulfonated oils and fats, as softeners for fibrous materials is well known, but in most instances the softeners of the prior art possess the disadvantage of being water soluble and are, therefore, readily washed out. Furthermore, most of the compounds used in the prior art do not possess suflicient compatibility with the thermosetting resins which are coming into such wide use in the textile field.

I have found that N-alkylol amides of fatty acids, and more especially the higher or long chain fatty acids are particularly suitable for use in the treatment of fibrous materials with thermosetting resins in order to improve the softness of the product. of the fatty acids may be represented by the type formula:

where R is an organic radical, R1 is hydrogen or an organic radical and a: and y are integers.

The following table shows the composition of various syrups used for crease proofing fabrics. The cream was a paste of an unpolymerized methylol urea-formaldehyde resin containing about 56% of resin solids, the remainder being water. The accelerator used was a mixture containing 88% diammonium phosphate and 12% hexamethylene tetramine.

Table I Softener y p Accel- Cream Water No. erator ype Percent in syrup Per cent Per cent Per cent 1 16.67 83.33 0.29 2 25.00 75.00 0.44 Sutlfonated oil mixure. 3 18.70 81.30 0.33 sitlfonated oil mixure. 4 25.00 75.00 0.44 Sulfonated castor oil. 5 17.70 82.30 0.31 Sulfonated castor oil. 6 25.00 75.00 .044 N-et han0l steer am e. 7 16.07 83.33 0.29 N-ethanol stearamide. 8 25.00 75.00 0.44 N-ethanol oocoanut fatty ecidamide. 9 10.67 83.33 0.29 N-ethanol ooooanut fatty acidamide. 10 25.00 75.00 0.44

The acidamides used in syrups 69 inclusive were dissolved in isopropanol. In the preparation of syrups Nos. 6 and 7 one part of N-ethanol stearamide is dissolved in 1.3 parts of warm isopropanol. In the preparation of syrups Nos. 8 and The N-alkylol amides .9 one part of N-ethanol cocoanut fatty acidamide is dissolved in 2.5 parts of warm isopropanol. In the preparation of these four syrups, each of these isopropanol solutions is mixed with an equal part of water to form a paste and the paste is then added to the other ingredients of the syrup.

Example 1 A series of samples of red cloaking (25% rayon-75% wool) was crease proofed with the syrups shown in Table I. After drying, the samples were washed in a solution containing 0.25% soap and 0.25% soda ash. After drying, the samples were compared for softness (hand). The original was rated zero, a. harsh hand was rated and a soft hand rated The figures given in the following table are comparative as to the degree of harshness or softness.

Before After washing Syrup No. washing, Hand mam Resin Fixation cent Per cent Per cent 9. 6 7. 4 77 --1O 11. 9 8. 0 67 '5 9. 8 6. 7 68 -5 l5. 2 9. 3 61 0 10. 4 5. 5 53 0 11. 1 8.0 72 +5 6. 5 4. 7 72 +5 11. 1 8. 3 75 -5 5. 7 3. l 54 -5 14. 5 6.8 47 l5 Example 2 A series of samples of brown cloaking (25% rayon-75% wool) were similarly crease proofed with the syrups listed in Table I, dried, washed and compared for softness in the same manner as in Example 1. The following results are obtained:

Before After washing Syrup No.- washing, Hand res: Resin Fixation Per cent Per cent Per cent 8. 3 5. 8 70 10 13. 2 10. 3 78 10 ll. 2 7. 3 65 1O 14. 8 8. 9 6O -5 11. 5 7.0 61 -5 12. 6 10.0 79 5 9. 0 6. 5 72 -5 10. 2 8. 0 78 0 6. 9 5. 0 85 0 l5. 6 9. l 58 l0 Example 3 the fabric. Sihe results obtained were entirely similar to those obtained in Example 2. The substitution of the insoluble soap for part of the amide did not appear to change the softening effect appreciably. Furthermore, the permanency of the impregnation appeared to be equally good and the water repellancy was much superior.

It has been found that up to about 50% of the softener may be replaced with the insoluble metal soaps without decreasing the permanency of the impregnation. More than about 50% of the insoluble soap is not generally suitable since the product does not possess the same degree of softness and furthermore, the greater quantity of soap may be incompatible with the resin syrup.'

Among the examples of other acidamides which are useful as softeners there are the N-alkylol amides of caproic, caprylic, capric, lauric, myristic, palmitic, oleic and stearic acids or any suitable mixtures of acids. The alkylol groups may 'be methanol, ethanol, isopropanol, butanol, etc. Furthermore, the amides may be prepared directly from oily.0r fatty materials such as tallow, palm oil, cocoanut oil, hydrogenated tallow, etc. The N-alkylol amides which have low water solubility are preferred inasmuch as they have a more permanent and lasting effect.

The N-alkylol amides used in the practice of the present invention may be prepared in any suitable manner. One way by which these compounds may be prepared is by the reaction of an acid chloride and a monoalkylol amine in thepresence of alkali, e. g. sodium hydroxide. The following example is illustrative of this process:

Example 4 To a mixture of 1 mol of monethanolamine' and 1 mol of sodium hydroxide (in a 20% aqueous solution), 1 mol of stearyl chloride is added slowly with agitation. The N-ethanol stearamide is separated by filtration, washed and dried. It may then be used as described above.

Among the resins which aresuitable for use in crease proofing fabrics and with which the softeners disclosed herein may be used are those resins containing reactive methylol groups. Examples of such resins are urea-formaldehyde, thiourea-formaldehyde, dicyandiamide-formaldehyde, phenol-formaldehyde, melamine-formaldehyde, and mixtures of these. Furthermore, the resins may be'modified or mixed with locust bean gum, sodium alginates, starches, gums, etc.

The N-alkylol fatty acidamides are especially suitable as softeners for materials impregnated with thermosetting resins because of the high de-' gree ofpcompatibility with these resins. 'Furthermore, many-of these amides are only slightly soluble in water and, therefore, do not wash out readily. On the other hand, softeners such as the sulfonated oils not only wash out readily but also tend to emulsify and remove the crease ture containing an N-alkylol amide of a higher fattyacid and a thermosetting resin selected from the group consisting of urea-formaldehyde resins, thiourea-formaldehyde resins, dicyandiamide-formaldehyde resins, melamine-formaldehyde resins and mixtures thereof.

2. A fibrous material impregnated with a mixture containing an N-alkylol amide of a fatty acid containing more than five carbon atoms and a thermosetting resin-selected from the group consisting of urea-formaldehyde resins, thloureaformaldehyde resins, dicyandiamide-formaldehyde resins, melamine-formaldehyde resins and mixtures thereof.

3. A fibrous material impregnated with a mixture containing an N-ethanol amide of a higher fatty acid and a thermosetting resin selected from the group consisting of urea-formaldehyde resins. thiourea-formaldehyde resins, dicyandiamideformaldehyde resins, melamine-formaldehyde resins and mixtures thereof. v

4. A fibrous material impregnated with a mix ture containing a urea-formaldehyde resin and N -ethanol stearamide.

5. A fibrous material impregnated with a mixture containing a melamine-formaldehyde resin and N-ethanol stearamide.

6. A fibrous material impregnated with a mixture containing the N-alkylol amides of the mixed acids of a natural fat glyceride,.-a nd a thermosetting resin selected from the group consisting of urea-formaldehyde resins, thiourea-formaldehyde resins, dicyandiamide-formaldehyde resins, melamine-formaldehyde resins and mixtures thereof.

7. A fibrous material impregnated with a mixture containing an N-alkylol amide of a higher fatty acid, a substantially water-insoluble soap and a thermosetting resin selected from the group consisting of urea-formaldehyde resins,

thiourea-formaldehyde resins, dicyandiamideformaldehyde resins, melamine-formaldehyde resins and mixtures thereof.

8. A fibrous material impregnated with a mixture containing a urea-formaldehyde resin, N-ethanol stearamide and one of the group consisting of aluminum stearate and zinc stearate.

9. A process of crease proofing and increasing the water repellency of fibrous materials which comprises treating said material with a solution dehyde resins, thiourea-formaldehyde resins,

dicyandiamide-formaldehyde resins, melamineformaldehyde resins and mixtures thereof.

11. A process of crease proofing fibrous materials which comprises treating said materials with a mixture containing a urea-formaldehyde resin and N-ethanol stearamide.

12. A process of crease proofing fibrous materials which comprises treating said materials with a mixture containing a melamine-formaldehyde resin and N -ethanol stearamide.

PAUL C. SCHROY. 

